Method for crimping cellulosic fibers and crimped cellulosic fibers obtained thereby

ABSTRACT

A method for manufacturing crimped yarns comprising cellulosic fibers, which comprises imparting distortion for a crimping treatment to a yarn comprising cellulosic fibers, subjecting the yarn to a caustic alkali treatment and a resin finishing treatment for imparting wet crease resistance. The crimped cellulosic yarns obtained thereby, and knitted or woven fabrics made of these crimped yarns.

United States Patent 1191 Hiroi et a1.

[451 Aug. 26, 1975 1 1 METHOD FOR CRlMPlNG CELLULOSIC FIBERS AND CRIMPEDCELLULOSIC FIBERS OBTAINED THEREBY [30] Foreign Application PriorityData July 19, 1972 Japan 47-72963 May 4, 1973 Japan 48-50014 [52] U.S.C1. 57/153; 8/125; 28/7216; 57/164 [51] Int. Cl. D02g 3/40 [58] Field ofSearch 57/164, 157 MS, 157 TS, 57/153; 28/721, 75 R, 75 WT, 72.16; 8/125[56] References Cited UNITED STATES PATENTS 2,449,215 9/1948 Goldthwaitct 211. 57/164 3,285,690 11/1966 Cooper, Jr. ct a1 57/164 X 3,330,0187/1967 Silver ct a1 28/7216 3,377,163 4/1968 Hamalainen et a1 57/1643,703,351 11/1972 Lock 28/75 R X 3,722,204 3/1973 lsirkcl et a1. 57/164OTHER PUBLICATIONS Ried et al., Effect of Mercerization & Tension onProperties of Wash-Wear Cotton; Nov. 1963; American Dyestuff Reporter,Vol. 52, No. 24, pp. 29-31. Reeves et al.; Durable Creases Produced inCotton & Resin Finished Cotton Fabrics by an Alkali Process; Oct. 1959;American Dyestuff Reporter, Vol. 48,'No. 21; pp. 43-46, 50.

Primary ExaminerJohn W. Huckert Assistant Examiner-Charles GorensteinAttorney, Agent, or Firm--Sughrue, Rothwell, Mion, Zinn and Macpeak [57]ABSTRACT A method for manufacturing crimped yarns comprising cellulosicfibers, which comprises imparting distortion for a crimping treatment toa yam comprising cellulosic fibers, subjecting the yarn to a causticalkali treatment and a resin finishing treatment for imparting wetcrease resistance. The crimped cellulosic yarns obtained thereby, andknitted or woven fabrics made of these crimped yarns.

6 Claims, No Drawings METHOD FOR CRIMPING CELLULOSIC FIBERS AND CRIMPEDCELLULOSIC FIBERS OBTAINED THEREBY BACKGROUND OF THE INVENTION 1. Fieldof the Invention This invention relates to a method for manufacturingcrimped cellulosic fibers so as to impart durable crimps and excellentcrimp-recovery characteristics to such fibers. Also, the inventionrelates to crimped cellulosic yarns obtained by this crimping method,and knitted or woven fabrics made of said crimped yarns.

2. Description of the Prior Art Crimped yarns have been widely used forvarious apparel uses because of their unique stretchability, bulkinessand feel, and various crimping methods have been proposed previously.For example, synthetic fibers are mechanically crimped, and thenheat-set, by utilizing their thermoplasticity. Or a method is employedin which synthetic fibers composed of two components which are differentin their stretching and shrinking behaviors are crimped by stretching orheat-shrinking them. These methods give comparatively good crimps tosynthetic yarns by dint of the thermoplastic characteristics of theresins that constitute the fibers. These methods, however, are naturallyinapplicable to cellulosic fibers which have quite differentcharacteristics. Even if the cellulosic fibers are processed by suchmethods, the crimps obtained are only temporary.

With a view to solving this problem, there was proposed a method whichcomprisesstrongly twisting a cellulosic yarn, weaving or knitting thetwisted yarn, and then treating the resulting woven or knitted fabricwith hot water or caustic alkali. According to this method, however, thedegree of crimp is limited by the number of twists, and good crimpscannot be obtained. Also, the crimp-recovery characteristics and crimpdurability of the crimped cellulosic yarn is of extremely low degrees,and the crimps are liable to disappear even by slight tension. A furtherdefect is that the resulting woven or knitted fabric exhibitsnon-uniformity owing to irregularities in crimps of the component yarns.Thus, no satisfactory method has yet been realized for crimpingcellulosic fibers, and no commercially feasible crimped cellulosicfibers have ever been provided. We have assiduously worked for removingthese defects, and completed the present invention.

An object of this invention is to provide a method for manufacturingcrimped cellulosic fibers to impart durable superior crimps andcrimp-recovery characteristics thereto without appreciably reducingtheir tenacity. It is a further object of this invention to providecrimped cellulosic yarns processed by said method, and also woven andknitted fabrics composed of said crimped cellulosic yarns.

SUMMARY OF THE INVENTION This invention provides a method formanufacturing crimped yarns comprising cellulosic fibers, whichcomprises imparting distortion for crimping treatment to said yarns,subjecting the yarns to a caustic alkali treatment and a resin finishingtreatment for imparting wet crease resistance, crimped cellulosic yarnsobtained by said method; and knitted and woven fabrics composed of thesecrimped yarns. These crimped yarns and knitted and woven fabrics havethe useful property of instantaneously regaining their crimps uponpassing water when the crimps are reduced.

DETAILED DESCRIPI" ION OF THE INVENTION The yarns comprising cellulosicfibers as used in the present invention are those obtained by spinningcellulosic fibers alone such ascotton, flax or viscose fibers, mixturesthereof, or mixtures of these cellulosic fibers with other fibers.Examples of the other fibers are polyester, polyamide or celluloseacetate fibers. The mixspun yarns of the cellulosic fibers and the otherfibers contain at least 50% by weight of the cellulosic fibers. Eventhose mix-spun yarns which contain less than 50% by weight of thecellulosic fibers can be processed into good crimped yarns by properlycombining the crimping method of this invention with the conventionalmechanical crimping method. Twisting at the time of spinning may be ofthe same degree as is usually practised, and it is not particularlynecessary to impart strong twisting. Depending upon the purposeintended, the twist is either lose or strong.

For imparting distortion, the expedients used for producing conventionalcrimped yarns are generally applicable. Means for imparting distortionby twisting the yarn and means for imparting distortion by knitting theyarn are especially preferred. The stuffer box method and the gearmolding method by which to impart toothed configurations to the yarn bya heated gear can also be employed, but where these methods areemployed, the distortion imparting step is carried out during the alkalitreatment or resin finishing treatment. Twisting is effected by twistingtwo or more single yarns by using a conventional twister. The number oftwists employed at this time is about 10 to 50 per inch. If the numberof twists is less than 10, good crimps are not obtained, and if itexceeds 50, the yarns tend to break. Preferably, the number of twists isat least 20 per inch, more preferably 30 to 40 per inch.

Where distortion is imparted by knitting, the yarn .may be knittedeither into a weft knitted fabric or warp knitted fabric. However, sincethe warp knitted fabric is produced from a number of yarns that havebeen warped, it is somewhat difficult to deknit the long yarnscontinuously, and therefore, the weft knitted fabric is preferred in thepresent invention. The texture of the knitted fabric may be of a plainstitch, interlock stitch or tuck stitch. In order to obtain onecontinuous yarn, a knitted fabric of the plain stitch made of one yarnis advantageous. I

In case of imparting distortion to the yarn by twisting or knitting, theresulting twisted yarn or knitted yarn is detwisted or deknitted afteralkali treatment and resin finishing treatment.

The sequence of the alkali treatment and the resin finishing treatmentis optional. From the viewpoint of crimpability, better results areobtained generally by performing the alkali treatment first. However,the sequence can be freely chosen, and it is also possible to performthe alkali treatment during the course of the resin finishing treatment.

The alkali treatment can be effected by applying an aqueous solution ofan alkali hydroxide to a yarn which has been given distortion, forexample, a twisted yarn or knitted fabric by spraying or padding, and ifdesired, subjecting it to tension. The concentration of the alkalihydroxide in the aqueous solution is to 350 g/liter, preferably 200 to300 g/liter. If the concentration is lower than 100 g/liter, the degreeof crimps is low, and when such a yarn is formed into a knitted fabric,the product is substantially the same as that knitted from an uncrimpedyarn. Even when the resin finishing treatment is performed incombination, durable crimps cannot be obtained. On the other hand, ifthe concentration is in excess of 350 g/liter, no appreciably greatimprovement in the state of crimps, the durability of crimps andcrimp-recovery characteristics is obtained, and the cost of processingbecomes rather high. This therefore is disadvantageous in actualproduction. The alkali treatment is carried out at a temperature nothigher than 50C., usually at room temperature, and the time of contactof the yarn with the alkali is about 20 to 120 minutes. After thetreatment, the alkali hy-- droxide adhering to the yarn is removed bywashing with hot or cold water.

The resins that are used for the resin finishing treatment are the kindwhich imparts the fibers crease resistance in the wet state. Such aresin may, for example, be (1) compounds having in the molecule at leasttwo groups selected from -vinyl and epoxy groups, or compounds which areconvertible to compounds having at least two epoxy groups during theresin finishing treatment, (2) compounds having in the molecule at leastone vinyl or epoxy group and a methylol group, and (3) cloth finishingresins conventionally used for resin finishing in the wet state.

These compounds classified under l to (3) include compounds which havenot so high molecular weights as can be named resins, but forconveniences sake, they are also referred to as resins in the presentspecification and claims. Examples of the compounds 1 are divinylsebacate, allyl acrylate, diglycidyl ether, epichlorohydrin, andethylene oxide. Examples of the compounds (2) are monomethylolacrylamide, dimethylol acrylamide, monomethylol aminostyrene, anddimethylol aminostyrene. Examples of the compounds (3) include glyoxalresins, triazone resins, methylolated alkylene urea resins, andcarbamate resins.

The amount of the resin used is 0.5 to 15%, preferably 3 to based on theweight of the yarn. If the amount is less than 0.5%, durable crimpscannot be obtained, and crimp recovery in the wet state is poor. On theother hand, if it is larger than by weight, the tenacity of the yarn isreduced greatly, and the co'efficient of friction of the yarn increases.Furthermore, in case where the distortion is imparted to the yarn bytwisting or knitting, during detwisting or deknitting the resultingtwisted yarn or knitted yarn, the breakage of the yarn occurs frequentlyto reduce the productivity extremely. This, in turn, causes difficultyof weaving or knitting of the resulting yarn, and is likely to renderthe quality of the product commercially infeasible.

The resin finishing treatment is performed by dissolving or dispersingthe resin in a solvent, usually water,-and applying the solution ordispersion to a yarn in the amount described above by spraying, padding,roller coating or other means, and if desired, heat-treating the yarnunder conditions suitable for the resin used. This will be described ingreater detail below.

In the case of using the resin under l) above, such as divinyl sebacate,allyl acrylate or diglycidyl ether, the resin is dissolved or dispersedin water or a mixture of water and an alcohol or other organic solventsin a concentration of 0.5 to and the solution or dispersion obtained isapplied to the yarn in the amount indicated above. The yarn is thendried, and then allowed to react in alkalinity. The reaction inalkalinity is performed, for example, by immersing the yarn in sodiumhydroxide having a concentration of about 2 g/liter to l00 g/liter,preferably 20 to g/liter, and if desired, squeezing the yarn to apick-up of about 60 to 200% after immersion, and then allowing the yarnto stand in a high humidity atmosphere. In either case, the treatingtime is about 20 minutes to 2 hours, and the yarn is subsequently washedwith cold or warm water, and dried at a temperature not higher than C.

The amount of the resin to be applied to the yarn can be easilycontrolled by the concentration of the resin and the amount of thesolution or dispersion to be applied. For example, in the case of thepadding method, the amount to be applied of the resin can be adjusted toa pick-up of about 60 to 150 by squeezing the yarn with squeeze rolls,frequently used in the usual fabric processing. When the resins of thistype are used, the alkali treatment may be carried out before or afterthe resin finishing treatment, or between the application of the resinand its reaction in alkalinity, for example, in either case, noappreciable difference is observed.

When epichlorohydrin is used as the compound convertible to a compoundhaving at least two epoxy groups in its molecule during the resinfinishing treatment, an alkali metal salt of an organic acid isconjointly made present during the resin finishing treatment to convertepichlorohydrin to diglycidyl ether. When ethylene oxide is used, it isconverted to diglycidyl ether by adding an alkali hydroxide, ironchloride or tin chloride to the reaction system. Other treatingconditions are the same as described above.

In the case of using the resins under item (2), for example,monomethylol acrylamide, dimethylol acrylamide, monomethylolaminostyrene or dimethylol aminostyrene, an aqueous solution of such aresin in a concentration of about 0.5 to 25% by weight is applied to theyarn in the amount indicated above together with a suitable amount of acatalyst as in the case of the resin (1 above, and the yarn is thenpre-dried at about 60 to 100C., after which the yarn is heat-treated forl to 15 minutes at to C by using a suitable heat source such as aheating oven or heating roll. The cataly'st used for this purpose may,for example, be an acidic type, such as magnesium borofluoride,magnesium chloride or zinc nitrate, and the amount of the catalyst isabout 20 to 50% by weight based on the weight of the resin. When a resinof this type is used, excellent durable crimps can be imparted to theyarn whether the alkali treatment is performed before or after the resinfinishing treatment. In view of crimpability, somewhat better resultsare obtained by first performing the alkali treatment and then the resinfinishing treatment, but for commercial production, it is advantageousto perform the alkali treatment after the resin finishing treatmentbecause one washing step can be omitted.

In the case of the resin under classification (3 such as a glyoxalresin, triazone resin methylolated alkylene urea resins or earbamateresin, a mainly aqueous solution of the resin in a concentration of 0.5to 25% by weight is applied to the yarn in the same way as in the caseof the resins l j and (2). At this time, the pH of the solution must beadjusted to 25 by adding an acid such as acetic acid, hydrochloric acid,or phosphoric acid, or a salt composed of a strongly acidic weak basesuch as magnesium chloride or zinc nitrate. The amount of the solutionis such that the pick-up is 100 to 200% based on the yarn, because theyarn must be processed in the wet state. In the case of these resins,too, the crimp properties of the resulting yarn do not differ whetherthe alkali treatment is performed before or after the resin finishingtreatment. If, however, the alkali treatment is carried out first, thedyeability of the treated yarn is somewhat superior, and therefore, fordyeing purposes, this sequence of treatments is preferred.

The greatest feature of this resin finishing treatment is that the resinis intramolecularly crosslinked during the treatment to impart superiorwet crease resistance to the yarn. If a resin finishing treatment forimparting dry crease resistance were used instead of the resin finishingtreatment in accordance with this invention, it would be impossible toimpart durable crimps to the yarn. Furthermore, in this case, thetenacity of the yarn is reduced extremely, as in case where thedistortion is imparted to the yarn by twisting or knitting, duringdetwisting or deknitting the resulting twisted yarn or knit ted yarn,the frictional resistance of the surface of the yarn is great owing to alarge quantity of the resin adhered thereto, and the tenacity of theyarn is reduced more exceedingly. The feel of a knitted or woven fabricobtained from such a yarn is harsh and undesirable.

After performing the above-described alkali treatment and resinfinishing treatment, in case where the distortion is imparted to theyarn by twisting or knitting, a detwisting treatment or a deknittingtreatment is subjected to the resulting yarn, thereby to give crimpedcellulosic yarns having excellent durable crimps. This completes theentire method of the present invention.

The method of producing knitted or woven fabrics using the crimped yarnsobtained by the method of this invention, and the resulting productswill be described below.

Knitted or woven fabrics can be produced from the crimped yarns inaccordance with this invention using a conventional knitting or weavingmachine in a manner known per se.

The resulting fabrics may be formed into outer garments, but owing tothe elasticity ascribable to crimps, and the hygroscopicity oranti-static property of the cellulosic yarns, these fabrics are suitablefor making use as underwears or undershirts.

Knitting includes warp knitting and weft knitting. In the case of theweft knitting, the crimped yarn is.knit ted on a single jersey machine,circular knitting machine or full fashion knitting machine under theconventional conditions (the number of gauges l2 28, loop length about3.5 to 13 millimeters), and the resulting knitted fabrics are used forproducing various underwear. sport shirts, casual wears, socks, orgloves. In the case of the warp knitting, a tricot knitting machine orraschel knitting machine is used under the conventional knittingconditions. The resulting knitted fabrics are used for various kinds ofunderwears or casual WCUI'S.

Woven fabrics can be produced from the resulting crimped yarns by anyconventional weaving machine under the conventional conditions. Wovenfabrics of various textures such as plain weave, sateen weave orBurberry weave. However, in view of the characteristics of the crimpedyarns, plain weave fabrics are preferred, and these fabrics can be usedas towels or mats in addition to underwears.

The crimp characteristics and crim-recovery characteristics of thecrimped yarns obtained in accordance with the method of this inventionare superior both in the dry and wet states. The greatest characteristicof the crimped yarns is that when their crimps are apparently reduced asa result of placing the yarns under tension for prolonged periods oftime, the original crimps and crimp-recovery characteristics can beregained to a considerable degree upon removing the tension, and whenthe yarns are dipped in water, preferably warm water, almost the samecrimped state as in the original state can be attained instantaneously.Usually, the crimped yarns obtained after the treatments of thisinvention are wound up on a skein, cone or cheese. Even when they arewound up under tension on a cone or cheese and stored for a long time,the original crimps of the yarns can be regained by unwinding them fromthe cone or cheese and thus placing them in the tension-free state. Thecrimps can also be regained by dipping the yarn in cold or warm water.Furthermore, the original crimps can be developed by first weaving orknitting the crimped yarns and then dipping the woven or knitted fabricin cold or warm water. Accordingly, when woven or knitted fabrics are tobe produced from the crimped yarns obtained by the method of thisinvention, it is almost unnecessary to pay attention to the yarn tensionin the woven or knitted goods. Even if crimps disappear apparently, theyare instantaneously developed on clipping the knitted or woven fabricsin cold or warm water. This markedly enhances the operability andproductivity of knitting and weaving. On the other hand, when a garmentproduced from such a knitted or woven fabric consisting of the crimpedyarns of this invention suffers from reduced crimps during wearing, thecrimps can be regained by dipping it in warm or cold water or by washingit. Thus, the crimp properties of the yarns of this invention areepochmaking in practical applications. In view of the fact that washingis essential in the apparel fields, it will be understood that thepresent invention is very advantageous for practical applications.

This unique advantage of this invention can be attained by a combinationof the alkali treatment and the resin finishing treatment for impartingwet crease resistance which have been described above. Another advantageof the present invention is that since the crimped yarns obtained by themethod of this invention have gone through the alkali treatment and theresin has been cross-linked in the fiber molecules of the yarns in thewet state, the resin is more uniformly caused to act on the fibers thanin the case of a resin finishing treatment for imparting dry creaseresistance. The alkali treatment in accordance with this inventionfurther contributes to good dyeability of the resulting crimpedcellulosic fibers. Furthermore, since the adhesion of the unreactedresin to the yarn is far more reduced, the tenacity of the yarn is notreduced appreciably, and the dyeability of the yarn is not impaired atall.

Thus, the method of this invention makes it possible to impart goodcrimps of superior durability to a yarn consisting essentially ofcellulosic fibers, and has high commercial value.

The following non-limiting Examples illustrate the invention in greaterdetail. In the Examples, the tenacity, the percentage crimp, and thecrimp recovery have been measured by the following methods.

1. Tenacity Measured in accordance with the method stipulated in .118L1008-1959. This tenacity is the tenacity at break (g) measured by aconstant rate tension-type tester at a pull speed of 30: 2 cm/min. lnthis case, the length of the sample used is 5 cm, and an initial loadcorresponding to 250 m of the same kind of yarn is exerted.

2. Percentage Crimp 50 wales of a sample knitted fabric are deknitted.One end of the sample yarn is fixed, and the sample yarn is hung byexerting a load of 0.1 g. The length (1,) of the yarn at this time ismeasured. Then, an additional 5 g load is exerted (total of 5.1 g), andthe length (l) of the sample yarn at this time is measured. Using thesevalues, the percentage crimp is measured from the following equation.

3. Crimp recovery 50 wales of a sample knitte'd fabric are deknitted.One end of the sample yarn is fixed, and the sample yarn is hung byexerting a load of 0.1 g. The length (l,,) of the sample yarn at thistime is measured, and then an additional 5 g load is exerted (total of5.1 g). After allowing the yarn to stand in this state for one minute,the length of the sample yarn is measured. Then, the 5 g load isremoved, and the sample yarn is allowed to stand for 1 minute under aload of 0.1 g. The length of the sample yarn at this time is measured.The crimp recovery of the yarn is calculated from the following equationusing these values.

Crimp recovery X 100 The wet crimp recovery shown in the Examples wasobtained by performing the above procedure in water at 20C.

EXAMPLE 1 The following tests were performed on a plain stitch knittedfabric of 60 count cotton ply yarns knitted in 21 courses/inch on a24-gauge knitting machine.

1. The sample was dipped for 1 minute in a 200 g/liter aqueous solutionof sodium hydroxide without changing the density of its texture, washedwith warm water and cold water to remove the sodium hydroxidecompletely, and then dried. The treated sample was designated Sample 1.

2. The sample was dipped in a mixed resinous liquor :omprising ofdimethylol dihydroxy ethyleneurea, 2% of zinc nitrate and 2% of apolyoxyethylene type ;oftener, and squeezed to a pick-up of 70% based on:he weight of the knitted fabric. It was then dried, heat- .reated at150C for 3 minutes, washed with warm water, and then dried. The treatedsample was designated Sample 2.

3. The sample was dipped in a 10% aqueous solution of dimethyloldihydroxy ethylene urea (adjusted to pH 3 with hydrochloric acid),squeezed to a pick-up of 150% based on the weight of the sample,maintained in a high humidity atmosphere at room temperature for 2hours, well washed with water, and dried. The treated sample wasdesignated Sample 3.

4. The sample was dipped in a 6% aqueous solution of glycidyl ether,squeezedto a pick-up of based on the weight of the knitted fabric,dried, clipped in a 50 g/liter aqueous solution of sodium hydroxide,squeezed to a pick-up of allowed to stand for one hour in a highhumidity atmosphere, washed with warm water to remove the alkalicompletely, and then dried. The treated sample was designated Sample 4.

5. The sample subjected to the alkali treatment as in (1) above wassubjected to the treatment described in (2) above. The treated samplewas designated Sample 5.

6. The sample subjected to the alkali treatment as in (1) above wassubjected to the treatment described in (3) above. The treated samplewas designated Sample 6.

7. The sample subjected to the alkali treatment as in (1) above wassubjected to the treatment described in (4) above. The treated samplewas designated Sample 7.

8. The sample which was first subjected to the resin finishing treatmentas in (4) above was then subjected to the alkali treatment as in (1)above. The treated sample was designated Sample 8.

9. The sample was dipped in a 6% aqueous solution of diglycidyl ether,squeezed to a pick-up of 80% based on the weight of the knitted fabric,dried, dipped in a 200 g/liter aqueous solution of sodium hydroxide for1 minute, washed thoroughly, again dipped in a 50 g/liter aqueoussolution of sodium hydroxide, squeezed to a pick-up of 100%, allowed tostand in a high humidity atmosphere for 1 hour, washed with warm waterto remove the alkali thoroughly, and dried. The treated sample wasdesignated Sample 9.

Each of the .above 9 Samples and the untreated sample were deknitted andwound up on a skein with a very small tension. The tenacity, percentagecrimp, crimp recovery, and wet crimp recovery of the resulting yarnswere measured. Furthermore, each of the samples were deknitted and werewound up on a cone under a relatively high tension, [at the time ofdeknitting], and allowed to stand in the wound state for 3 months. Thecrimp characteristics of the yarn which was unwound after 3 months fromthe cone were determined. Also,- such unwound yarns were dipped for 1minute in water at 40C, and air dried, and then the crimpcharacteristics of these yarns were examined. The results are shown inTable 1.

TABLE 1 Properties of yarns after Crimp characteristics after winding upon treatment cones and stored for 3 months Sample Tcna- Pcrcen- CrimpWet After unwinding After warm water treat- No. city tage rcc0 crimp(before warm mcnt and air drying crimp very recn- Wiltfil treatment) Ivery Run (g) ("/1 ('71) Pcrcen- Crimp Percen- (rimp Wet Nov Ingerecolzlgc recocrimp crimp very crimp very reco- (7:) (70) fl) y( 1 1 39450.3 58.6 10.x 5 7(1 7 t 70 18 Z. 2 2411 44.4 (v4.7 37.3 11) 7X 25 (144O Properties of yarns after Crimp characteristics after winding up ontreatment cones and stored for 3 months Sample Tena- Perccn- Crimp WetAfter unwinding After warm water treat- No. city tage recocrimp (beforewarm ment and air drying crimp very recowater treatment) very Run (g)(7? ("/1 (71 Percen- Crimp Percen Crimp Wet No. tage recorage recocrimpcrimp very crimp very recoyU d 3. 3 380 31.2 43.1 30.5 i 80 28 40 47 4.4 350 30.8 25.2 46.7 4 80 3O 25 45 5. 5 259 47.8 65.1 44.3 8O 28 67 516. 6 365 58.9 64.7 55.2 26 80 58 64 55 7. 7 378 61.3 64.8 57.5 28 82 6065 58 8. 8 370 60.7 65.0 58.2 27 81 60 66 58 9. 9 373 59.6 65.2 58.4 2680 59 66 59 10. 423 19.6 20.3 5.3 l 90 0 Original untrcutcd fabric As isclearly seen from Table l, in the crimped yarns obtained in accordancewith this invention, the tenacity of the yarn is not appreciablyreduced, and its crimp characteristics are well balanced. Even when thecrimp are reduced under tension, they return almost to the original onlyby immersing the yarn in warm water for a very short time. A comparisonof Samples Nos. 7, 8 and 9 shows that the sequence of the alkalitreatment and the resin finishing treatment is optional, and that whenthe yarn is reactive in alkalinity as in the case of the yarn of thisinvention, the alkali treatment may be performed during the resinfinishing treatment, as in Run No. 9. On the other hand, even if thealkali treatment is conjointly employed with a resin finishing treatmentfor imparting dry crease resistance, the effect as is seen in the methodof this invention cannot be obtained, as shown in Run No. 5.incidentally, Sample 5 could not be smoothly deknitted with some hitchedfeel. However, in Run No. 6 in which the same resin was used forfinishing treatment but the treatment was performed in the wet state andthe alkali treatment was also performed, good crimp properties wereobtained.

A plain stitch knitted fabric was produced by a gauge single jerseyknitting machine using each of the crimped yarn Samples Nos. 1, 4, 7, 8and 9 which was wound on a cone. The resulting knitted fabric was washedwith water and air dried. The texture was 30 wales/40 courses.

A long sleeve undershirt was sewn from the knitted fabric, and a wearingtest was performed. In the test, the shirt was worn for two days andthen washed, and this cycle was repeated for 3 months. The washing wasmade by a jet stream type household washer. Washing was conducted for 15minutes, and rinsing was effected three times consuming 10 minutes eachtime. Then, the shirt was centrifugally dehydrated, and air dried at 50to 60C.

As a result, shirts made of the knitted fabrics using the crimped yarnsof Samples Nos. 7, 8 and 9 (present invention) hardly showed stretch orloosening even at the elbow portions which usually underwent vigorousstretching and bending. but fitted to the body very well during a twodays wearing. in addition, by washing, the crimp characteristicssubstantially returned to the original state. After a lapse of threemonths, there was no appreciable change in fitting and stretchingproperties. When these shirts were worn continuously for 10 days afterthis 3 month period, the fitting properties of the shirts were reducedsomewhat at the elbow portions, and the shirts stretched by about 1.2 to1.4% around the waist but the fitting properties were still good. Bysubsequently washing the shirts, the elbow portions returned almost tothe original, and the waist showed a stretch of about 0.5% which waswithin the range of measuring error. The shirts gave wearing comfortbecause they had superior hygroscopicity and were free from staticcharge owing to their cellulosic fiber constituents. 1n the case ofSamples 1 and 4, the stretchability was poor, and there was greatloosening during wearing. Furthermore, there was hardly any crimprecovery by washing.

A plain weave fabric was produced from Sample 7 using a conventionalweaving machine. After washing with water and drying, the density of thewoven fabric was I32 warps/inch and 106 wefts/inch. When it was used asa towel, it exhibited unique feel and excellent water imbibition.

EXAMPLE 2 The same knitted fabric as used in Example 1 was used andaqueous solutions of monomethylol acrylamide in various concentrationswere applied by padding to the fabric in the amounts indicated in Table2, and squeezed to a pick-up of The treated fabric was dried at 100C,and heat-treated for 3 minutes at C. In this procedure, zinc nitrate wasused as a catalyst in an amount of 1/10 of the weight of the resin.Then, the fabric was dipped in an aqueous solution of sodium hyroxide invarious concentrations shown in Table 2, washed with water, and dried.Each of the knitted fabrics so treated was deknitted in the same way asin Example Land wound 'up on a skein under a very small tension, or on acheese under relatively high tension. The same properties as shown inExample 1 of these yarns were'measured, and the results are shown inTable 2. The temperature of water used for a warm water treatment was24C.

TABLE 2 Amount Alkali Properties of yarns after Crimp characteristicafter winding up of contreatment on cones and stored for 3 months resincentra tion Tena' Percen- Crimp Wet After unwinding After watertreatment city tage recocrimp (before water and air drying crimp veryrecotreatment) very Run (g/l) (g) ("/1) (71) ('7!) Percen- Crimp PcrccnCrimp Wet No. tage recotage recocrimp crimp very crimp very reco- (7(71) v yWr) Original untreated cloth It is seen from Table 2 that goodresults are obtained with suitable ranges of the amount of the resin tobe applied and the alkali concentration used in the caustic and dried.These knitted fabrics were deknitted to obtain various kinds of yarns.The properties of these yarns were measured in the same way as inExample 1,

alkali treatment, and that superior durability of crimps and the resultsobtained are shown in Table 3.

TABLE 3 Amount Alkali Properties of yarns after Crimp characteristicafter winding up of contreatment on cones and stored for 3 months resincentra- 7 tion Tena- Percen- Crimp Wet After unwinding After warm watertreatcity tage reco- Crimp (before warm ment and air drying v crimp veryrecowater treatment) Run (g/l) (g) very Percen- Crimp Percen- Crimp WetNo. tage recotage recocrimp crimp very crimp very reco- 1. 0.3 250 38348.0 58.3 17.4 i 5.6 70.3 8.1 70.8 60.5 2. 0.7 250 378 44.7 60.5 38.220.1 80.7 40.3 43.5 38.9 3. 3.0 250 374 46.2 62.3 43.1 21.6 80.9 45.044.7 42.7 4. 6.0 365 26.4 29.8 48.7 20.8 38.4 20.8 25.4 35.6 5. 6.0 120370 47.8 38.6 55.8 26.4 80.5 46.6 g 46.3 51.3 6. 6.0 200 372 60.0 65.359.5 28.1 81.3 58.3 58.4 59.2 7. 6.0 300 370 60.1 65.3 59.6 28.5 81.358.4 58.4 59.2 8. 6.0 400 361 r 60.3 65.3 57.2 28.7 80.6 58.7 58.6 57.69. 12 250 320 61.2 68.6 59.3 29.3 81.7 59.0 59.0 59.5 10. 18 250 28061.5 68.3 59.5 29.3 81.0 59.3 59.0 59.0 11.* 423 19.6 20.3 5.3 1 0Original untreated fabric can be obtained only by a combination of thesetreatments within the suitable concentration ranges.

EXAMPLE 3 Using the same knitted fabric as in Example 1 and di glycidylether as a resin for the resin finishing treatment, various treatedknitted fabrics were obtained by varying the amount of the resin appliedand the concentration of the caustic alkali in the same way as inExample 2. In this Example, diglycidyl ether was applied as an aqueoussolution of various concentrations, and the squeezing was performed to apick-up of 100%. After drying, the treated knitted fabric was dipped inan aqueous solution of sodium hydroxide of various concentrations asshown in Table 3, washed with water, and then dried. Then, the fabricwas further dipped in a 50 g/liter aqueous solution of sodium hydroxide,and squeezed to a pick-up of 100%, followed by allowing to stand for onehour in a high humidity atmosphere (a chamber held at a humidity ofabout to spraying water). The treated fabric was washed with warm waterand cold water to remove the alkali completely.

It is seen from Table 3 that good results are obtainable with theglycidyl ether type resin being in a concentration of about 0.5 to 15%,and good durability of crimps can be obtained only by performing thecaustic alkali treatment in suitable concentrations within this range.

EXAMPLE 4 A knitted fabric (21 courses/inch) was produced from a 85count mix-spun play yarn composed of 65% of cotton and 35% ofpolyethylene tcrephthalate using a 24-gauge knitting machine. Thisknitted fabric was treated as follows:

1.-The knitted fabric was dipped in a 6% aqueous solution of dimethyloldihydroxy ethyleneurea (adjusted to a pH 3 with hydrochloric acidsqueezed to a pick up of based on the weight of the fabric, andmaintained in a high-humidity atmosphere at room temperature for 2hours. Then, the fabric was dipped in a 250 g/litcr aqueous solution ofsodium hydroxide. washed with water. dried. and then deknitted. Theresulting yarn was designated Sample 1.

2. The knitted fabric was dipped in a 250g/1iter aqueous solution ofsodium hydroxide, washed, and subjectcd to the resin treatment in thewet state using the same resin as in the preparation of Sample 1. Thefabric It is seen from Table 4 that using any of the resins specified,good durable crimps can be obtained. It is clear from a comparison ofRuns Nos. 1 to 4 that when dimethylol hydroxy diethyleneurea is used,the crimp was well washed, dried, and then deknitted. The result 5properties of the yarns are much the same whether the ing yarn wasdesignated Sample 2. alkali treatment is performed before or after theresin 3. The above knitted fabric was dipped in a 6% aquefinishingtreatment, but in the case of monomethylol ous solution of monomethylolaminostyrene (using aminostyrene, somewhat better results are obtainedby 1.0% of zinc nitrate as a catalyst), squeezed to a pickperforming thealkali treatment first. up of 100% based on the weight of the knittedfabric, 10 dried at 100C, and heat-treated for 3 minutes at F 5 150C Thefabric was further dipped in a 50 g/liter A plain stitch knltted fabric(21 courses/inch) was aqueous solution of sodium hydroxide, squeezed toa prPduced from a Q i Ply yam of 50056 rayon pick-up of 100%, allowed tostand in a high humidity 3 kmttmg machme- The resultmg atmosphere for 1hour at room temperature, washed l5 ted fabrlc was pp in a Solutionconsisting of 6% of with water, and then dried. The fabric was thendipped monomethylol acrylamlde and 06% of Zmc "mate, q in a 250 g/literaqueous solution of sodium hydroxide, ueezed to a plck'up of 100% P at Cand washed with water, and deknitted The resulting yam then heat-treatedat 150C for 3 minutes. The treated was designated Samp|e 3 fabric wasdipped in a 130 g/liter aqueous solution of 4. [n the proceduredescribed in (3) above, the caussodium hydroxide for 1 mihute, Washedwith Warm tic alkali treatment was first performed, and then the Waterand Cold Water, and dekhltted, followed y Windresin finishing treatmentwas performed. The resulting lhg p the yam 0h 11 Skelh Under a y Smalltehsloh yam was designated Sample 4 thereby to form crimped yarns inaccordance with this 5. The above knitted fabric was dipped in a 250hg/liter aqueous solution of sodium hydroxide, dipped in 25 The crimpedyam had a tenacity of 340 g a Crimp a 6% aqueous solution of divinylsebacate, squeezed to Percentage of 605% a y Crimp recovery of 645%, apick-up of 100%, dried, dipped in a 50 g/liter aqueous and a wet crlmprecovery of solution of sodium hydroxide, squeezed to a pick-up ofFurthermore, at the tlme of dekhmihgr the y was 100%. allowed to standin a high humidity atmosphere wound up on a Cohe under Strong tehsiohiand allowed at room temperature for 1 hour, washed well with wato Standfor 3 months- The, the unwound y was ter, dried, and then deknitted. Theresulting yarn was tested as to its crimp characteristics. The yarnexhibdesignated Sample 5. ited a crimp percentage of 28% and a crimprecovery 6, The ab v k i d f b i was di d i a 250 of 81%. When the yarnwas clipped in water at 30C for g/liter aqueous solution of sodiumhydroxide, then 1 minute and air dried, it exhibited a crimp percentagedipped in a 6% aqueous solution of allyl acrylate (using 0f 60% and aCrimp recovery of which Values 0.6% of zinc nitrate as a catalyst),squeezed to a pickere most the same as the Original values. up of 100%,dried at 100C, and heat-treated for 3 minutes at 150C. The fabric wasthen deknitted. The EXAMPLE 6 resulting yum was d i d S l 6 Two 60-countpure cotton yarns twisted in the right- 7 Th same k i d f b i bj d to hSame handed direction at 30 turns/inch were given a final kali treatmentas described above was dipped in a 6% twist in the left-handed directionat 37 turns/inch [0 aqueous solution of dimethylol triazone (adjusted toa make a ply yarn. A predetermined length of the yarn pH 3 withhydrochloric acid), squeezed to a pick-up of was wound p n Skein, n usedas a sample. The 150%, maintained in a high humidity atmosphere for 2sample was treated s fOllOWSI hours at room temperature, washed withwater, dried, 1. The sample was dipped in a 200 g/liter aqueous soanddeknitted. The resulting yarn was designated Sam lution of sodiumhydroxide for 1 minute while mainple 7. taining the original length,washed with warm water The crimp characteristics of these seven kinds ofand cold water to remove the sodium hydroxide comyarns were measured inthe same way as in Example 1. pletely, and then dried. The treatedsample was desig- The results are shown in Table 4. nated Sample 1.

TABLE 4 Amount Alkali Properties of yarns after Crimp characteristicsafter winding up of cn1l treatment on cones and stored for 3 monthsresin centration Tenu- Pcrccn- Crimp Wet After unwinding After warmwater treatcity tage recocrimp (before warm ment and air drying crimpvery rccowater treatment) very Run ('77) (g/l) (g) (71) (711 (7(1Percen- Crimp Percen- Crimp Wet Nit tage recotage recocrimp crimp verycromp very reco- (71) (I) (7:1 ('71.) yt' 1. 9 250 254 50.5 04.3 01.524.4 x5e 414.3 63.0 59.2 2 0 250 252 52.1 04.4 61.7 25.1 145x 48.6 63.059.7 3. a 250 203 51.9 03.2 02.0 25.3 m1 495 62.8 58.9 4. (i 250 20053.7 03.5 02.2 25.x 86.3 49.7 03.1 59.4 5. 0 250 257 52.9 02,7 01.4 20.285.9 50.2 02.8 58.3 (i. t 250 259 51.5 05.0 61.x 20.7 x59 50.1 64.0 58.57. 9 250 251 51.4 04.2 61.9 25.x x 49.5 60.9 59.4 x,* 270 22.2 20.x 7.44.3 91.0 0

Original untreated fabric 2. The sample was dipped in a mixed aqueoussolution containing 10% of dimethylol dihydroxy 3. The sample was dippedin a 6% aqueous solution Each of the nine treated samples and theuntreated ply yarn sample was dctwisted by a twister, and the tenacity,percentage crimp, crimp recovery, and wet crimp recovery of theresulting yarns were measured.

Furthermore, each of the above samples was detwisted and wound up on acone under relatively strong tension, and allowed to stand for threemonths, followed by unwinding. The crimp characteristics of the unwoundyarns and those of the unwound yarns after of diglycidyl ether, squeezedto a pick-up of 80% based immersing in water for 1 minute at 40C and airdrying on the weight of the sample, dried, dipped in a 50 g/literaqueous solution of sodium hydroxide, squeezed Properties of yarns afterwere also examined. The results obtained are shown in Table 5.

TABLE 5 Crimp characteristics after winding up on cones and stored for 3months treatment Tena- Percen- Crimp Wet After unwinding After watertreatment city tage recocrimp (before water and air drying crimp veryrecotreatment) very Run (g) (7n) (7:) (7r) Percen- Crimp Percen- CrimpWet No. tage recotage recocrimp crimp very crimp very reeo' Control;original untreated yarn to a pick-up of 100%, allowed to stand in a highhumidity atmosphere for 1 hour, washed with warm water to remove thealkali completely, and dried. The treated sample was designated Sample3.

4. The sample was subjected to the alkali treatment in the same way asin 1 above, and then to the treatment described in (2) above. Thetreated sample was designated Sample 4.

5. The sample was dipped in a 10% aqueous solution of dimethyloldihydroxy ethyleneurea (adjusted to a pH 3 with hydrochloric acid),squeezed to a pick-up of 150%, maintained in a high humidity atmosphereat room temperature for 2 hours, well washed with water, and then dried.The treated sample was designated Sample 5.

6. The sample was subjected to the alkali treatment as in 1 above, andthen to the treatment described in (5) above. The treated sample wasdesignated Sample 6.

7. The sample was subjected to the alkali treatment as in 1 above, andthen to the treatment described in (3) above. The treated sample wasdesignated Sample 7.

8. The sample was subjected to the resin finishing treatment as in (3)above, and then to the alkali treatment described in 1 above. Thetreated sample was designated Sample 8.

9. The sample was dipped in a 6% aqueous solution of diglycidyl ether,squeezed to a pick-up of 80% based on the weight of the sample, dried,dipped in a 200 g/liter aqueous solution of sodium hydroxide, thoroughlywashed, then dipped in a 50 g/liter aqueous solution of sodiumhydroxide, squeezed to a pick-up of 100%, allowed to stand in a highhumidity atmosphere for 1 hour, washed with warm water to remove thealkali completely, and then dried. The treated sample was designatedSample 9.

1t is clearly seen from the results shown in Table 5 that in the presentinvention in which the alkali treatment and the resin finishingtreatment for imparting wet crease resistance are conjointly employed,the tenacity of the resulting crimped yarns is not appreciably reduced,and their crimp properties are well balanced, and especially when thecrimp characteristics are dete- 40 riorated under tension, the originalcrimp characteristics can be regained substantially merely by dippingthe yarns in water. A comparison of Samples 6, 7, 8 and 9 shows that thealkali treatment may be carried out either before or after the resinfinishing treatment, and

in the case of the alkali reaction type, the alkali treat ment may becombined in the process of resin finishing treatment as shown in Run No.(9). On the other hand, even if a resin finishing treatment intendedprimarily for imparting dry crease resistance is conjointly employed asin Run No. (4), the effects as shown in the present invention are notproduced. A comparison of it with Run No. (6) shows that it is importantto perform the resin finishing treatment for imparting wet creaseresistance. Incidentally, Sample 4 has a high coefficient of friction,and is difficult to dctwist uniformly.

EXAMPLE 7 The same sample as used in Example 6 was dipped in an aqueoussolution of monomethylol acrylamide of various concentrations to applythe resin in the amount indicated in Table 6. The treated sample wasdried at 100C, and heattrcated at 150C for 3 minutes. At this time,Zll'lC nitrate was used as a catalyst in an amount of H10 of the weightof the resin. The application of the resin was performed by padding, andsqueezing was made to a pick-up of Then, the sample was dipped in anaqueous solution of sodium hydroxide in the concentrations shown inTable 6, washed with water, and dried. The properties of the treatedsamples were measured in the same'way as in Example 6, and the resultsobtained are shown in Table 6.

tion of the caustic alkali. In the present Example, the yarn was dippedin an aqueous solution of diglycidyl ether in various concentrations,and squeezed to a TABLE 6 Amount Alkali Properties of yarns after Crimpcharacteristics after winding up of contreatment on cones and stored for3 months resin centration Tena- Pereen- Crimp Wet After unwinding Afterwater treatment city tage recocrimp (before water and air drying crimpvery recotreatment) very R 9%) (g/l) (g) 7r) (7: (7r percen- CrimpPercen- Crimp Wet Na tage recotage recocrimp crimp very crimp very reco-('7?) (7:) very(%) l. 0.3 250 399 37.l 59.5 20.3 3 81.3 9 80.2 28.2 2.0.7 250 394 40.8 7L8 52.3 20.0 68.5 36.5 56.5 60.5 3. 3.0 250 395 42.l72.9 59.6 25.5 67.8 38.3 57.2 65.8 4. 6.0 80 384 33.0 52.3 59.5 15.852.5 28.2 38.2 65.8 5. 6.0 I20 382 43.3 72.6 65.4 25.0 85.4 37.9 70.369.2 6. 6.0 200 382 43.3 74.4 68.1 25.2 83.2 38.2 70.9 69.0 7. 6.0 300386 43.0 74.5 69.3 25.8 85.1 38.2 7l.4 69.0 8. 6.0 400 380 44.0 7.2766.7 27.6 85.3 38.5 71.1 70.0 9. l2 250 383 44.6 73.3 69.5 27.2 86.238.7 71.2 68.0 l0. I8 250 340 45.3 73.] 69.8 27.2 86.l 39.0 72.8 69.2ll. 4l5 10.5 39.8 ll.3 l 90 0 Control; original untreated yarn It isseen from Table 6 that good results are obtained when the amount of theresin to be applied and the alkali concentration in the caustic alkalitreatment are 30 within suitable ranges. It is also clear thatespecially good durability of crimps can be obtained only by acombination of these treatments within suitable concentration ranges.

EXAMPLE 8 Two l00-count pure cotton yarns twisted in the righthandeddirection at 34 turns/inch were subjected to final twist in theright-handed direction at 40 turn- 35 yarn was then washed with warmwater and with cold water to wash out alkali completely, and dried. Theproperties of the treated yarns were measured in the same way as inExample 6, and the results are shown in Table 7.

TABLE 7 Amount Alkali Properties of yarns after Crimp characteristicsafter winding up of eontreatment on cones and stored for 3 months resincentration 'l'ena- Percen- Crimp Wet After unwinding After watertreatment city tage reccrimp (before water and air drying crimp veryrecotreatment) very Run (/1 (g/l) (g) (71 (7: (7r Pereen- Crimp Pereen-Crimp Wet No. tage recotage recocrimp crimp very crimp very reco- (71-)(V -J r) y( l. 0.3 250 235 28.0 68.7 22.4 4 82.3 10 8L3v 29.l 2. 0.7 250230 29.6 72.5 54.5 l7.2 69.4 37.3 58.7 M2 3. 3.0 250 229 30.5 74.6 58.725.5 68.8 39.2 60.3 65.8 4. 6.0 80 225 16.2 5L5 59.6 15.8 54.5 29.1 3865.8 5. 6.0 I20 230 36.5 76.6 66.8 26.2 85.9 32.4 65.6 69.7 6. 6.0 200230 40.7 78.3 69.5 25.4 83.7 35.9 66.2 69.8 7. 6.0 300 232 4] .0 78.369.7 26.0 85.2 36.8 66.8 69.3 8. 6.0 400 23] 41.0 77.2 65.9 27.6 85.036.8 67.l 69.0 9. I2 250 2l8 42.5 78.] 70.3 28.2 86.3 38.4 67.1 69.5 l0.-.l8 250 I71 42.8 78.0 70.3 28.2 86.l 38.3 75.2 80.2 I l. 270 l 1.2 40.5l2.8 l 92 0 Control; Original unrcneted \-:|rn

s/inch. A predetermined length of the resulting ply yarn was wound up ona skein, and used as a sample. Using diglycidyl ether the resin forresin-finishing. the yarn was subjected to various treatment by varyingthe amount of the resin to be applied. and the concentralt is seen fromTable 7 that the amount of the resin 5 is suitably about 0.5 to 15%, andespecially good durability of crimps can be obtained by performing thealkali treatment conjointly using an aqueous solution of an alkalihydroxide of suitable concentrations.

19 EXAMPLE 9 Two 85-count mix-spun yarns composed of 70% of cotton andof polyethylene telephthalate fiber twisted in the right-handeddirection at 32 turns/inch were subjected to final twist in theleft-handed direction at 38 turns/inch using a twister. A predeterminedlength of the resulting ply yarn was wound up on a skein, and used as asample. The sample was treated as follows:

l. The sample was dipped in a 6% aqueous solution of dimethyloldihydroxy ethyleneurea (adjusted to a pH 3 with hydrochloric acid),squeezed to a pick-up of 150% based on the weight of the sample,maintained in a high humidity atmosphere at room temperature for 2hours, subsequently dipped in a 250 g/liter aqueous so lution of sodiumhydroxide, washed with water and dried, followed by detwisting. Theresulting yarn was designated Sample 1.

2. The sample was dipped in a 250 g/liter aqueous solution of sodiumhydroxide, washed, and then subjected to the same resin finishingtreatment in the wet state using the same resin as used in Run No. 1above. The sample was then washed well with water, dried,

tion of sodium hydroxide, squeezed to a pickup of 100%, allowed to standin a high humidity atmosphere at room temperature-for 1 hour, thoroughlywashed with water, dried, and then detwisted. The resulting yarn wasdesignated Sample 5.

6. The sample was subjected to the same alkali treatment as above usinga 250 g/liter aqueous solution of sodium hydroxide, dipped in a 6%aqueous solution of allyl aerylate (using 0.6% of zinc nitrate as acatalyst), squeezed to a pick-up of 100%, dried at 100C, and thenheat-treated at 150C for 3 minutes, followed by detwisting. Theresulting yarn was designated Sample 6.

7. The sample was subjected to the alkali treatment in the same way asabove, dipped in a 6% aqueous solution of dimethylol triazone (adjustedto a pH 3 with hydrochloric acid), squeezed to 150%, allowed to stand ina high humidity atmosphere at room temperature for 2 hours, washed withwater, dried, and detwisted. The resulting yarn was designated Sample 7.

The crimp characteristics of these seven kinds of yarns were examined inthe same way as in Example 6, and the results obtained are shown inTable 8.

TABLE 8 Amount Alkali Properties of yarns after Crimp characteristicsafter winding up of contreatment on cones and stored for 3 months resincentration Tena- Per- Crimp Wet After unwinding After water treatmentcity centage recocrimp (before water and air drying crimp veryrccotreatment) very Run (g/l) (g) (71) Percen- Crimp Percen- Crimp WetNo. tage recotage recocrimp crimp very crimp very reco- Control;Original unreaeted yarn and detwisted. The resulting treated yarn wasdesignated Sample 2.

3. The sample was dipped in a 6% aqueous solution of monomethylolaminostyrene (using 1.0% of zinc nitrate as a catalyst), squeezed to apick-up of 100% based on the weight of the sample, dried at 100C, andthen heat-treated at 150C for 3 minutes. Then, the sample was furtherdipped in a g/liter aqueous solution of sodium hydroxide, squeezed to apick-up of 100%, allowed to stand in a high humidity atmosphere at roomtemperature for 1 hour, washed with water, and dried. Then, the samplewas dipped in a 250 g/liter aqueous solution of sodium hydroxide, washedwith water, dried, and detwisted. The resulting yarn was designatedSample 3.

4. ln Run No. (3), the sample was first subjected to the alkalitreatment, and then the same resin finishing treatment. The resultingyarn was designated Sample 4.

5. The sample was subjected to the alkali treatment in the same way asabove using a 250 g/liter aqueous solution of sodium hydroxide, dippedin a 6% aqueous solution of divinyl sebacate, squeezed to a pick-up ofdried, then dipped in a 50 g/liter aqueous solu- It is seen from Table 8that good durable crimps are obtained by using any of the resins. Acomparison of Runs Nos. (1 to (4) shows that when dimethylol dihydroxyethyleneurea is used, the crimp properties of the resulting yarns aremuch the same whether the alkali treatment is carried out before orafter the resinfinishing treatment, but in the case of monomethylolaminostyrene, somewhat better results are obtained by performing thealkali treatment first.

While the invention has been described in detail and with reference tospecific embodiments thereof, it will be apparent to one skilled in theart that various changes and modifications can be made therein withoutdeparting from the spirit and scope thereof.

What is claimed is:

l. A method for manufacturing crimped yarns consisting substantially ofcellulosic fibers and having durable crimps and excellent crimp-recoverycharacteristics in wet and dry states which comprises, in the listedorder, the steps of:

a. impartingdistortion to the yarn by knitting,

b. subjecting the knitted yarn to a resin finishing treatment forimparting wet crease resistance in a wet state with a compound selectedfrom the group consisting of monomethylol aminostyrene and monomethylolacrylamide in a concentration of about 0.5 to 25% by weight togetherwith a catalyst in an amount of about 20 to 50% by weight based on theweight of the resin.

drying the resin-treated yarn at a temperature of from 50 to 100C,

heat-treating the dried yarn at a temperature of from 130 to 150 for lto minutes,

subjecting the yarn to a caustic alkali treatment with an aqueoussolution of an alkali hydroxide in a concentration of 200 to 350 g/literat a temperature of not higher than 50C,

washing the yarn with water to remove the alkali hydroxide adhered tothe yarn,

1. A METHOD FOR MANUFACTURING CRIMPED YARNS CONSISTING SUBSTANTIALLY OFCELLULOSIC FIBERS AND HAVING DURABLE CRIMPS AND EXCELLENT CRIMP-RECOVERYCHARACTERISTICS IN WET AND DRY STATES WHICH COMPRISES, IN THE LISTEDORDER, THE STEPS OF: A. IMPARTING DISTORTION TO THE YARN BY KNITTING, B.SUBJECTING THE KNITTED YARN TO A RESIN FINISHING TREATMENT FOR IMPARTINGWET CREASE RESISTANCE IN A WET STATE WITH A COMPPOUND SELECTED FROM THEGROUP CONSISTING OF MONOMETHYLOL AMINOSTYRENE AND MONOMETHYLOLACRYLAMIDE IN A CONCENTRATION OF ABOUT 0.5 TO 25% BY WEIGHT TOGETHERWITH A CATALYST IN AN AMOUNT OF ABOUT 20 TO 50% BY WEIGHT BASED ON THEWEIGHT OF THE RESIN. C. DRYING THE RESIN-TREATED YARN AT A TEMPERATUREOF FROM 50* TO 100*C, D. HEAT-TREATING THE DRIED YARN AT A TEMPERATUREOF FROM 130* TO 150* FOR 1 TO 15 MINUTES E. SUBJECTING THE YARN TO ACAUSTIC ALKALI TREATMENT WITH AN AQUEOUS SOLUTION OF AN ALKALI HYDROXIDEIN A CONCENTRATION OF 200 TO 350 G/LITER AT A TEMPERATURE OF NOT HIGHERTHAN 50*C, F. WASHING THE YARN WITH WATER TO REMOVE THE ALAKALIHYDROXIDE ADHERED TO THE YARN. G. DRYING THE YARN, AND H. DEKNITTING. 2.The method of claim 1 wherein said catalyst is a member selected fromthe group consisting of magnesium borofluoride, magnesium chloride andzinc nitrate.
 3. Crimped cellulosic yarns obtained by the processclaimed in claim
 1. 4. A woven or knitted fabric comprising the crimpedcellulosic yarns obtained by the process claimed in claim
 2. 5. Themethod of claim 1 wherein the knitting is a weft knitting.
 6. The methodof claim 1 wherein the knitting is a plain stitch knitting.